Thionyl Chloride → HCID 14802114, compound

HRID 329722Notes

Reaction equation

HRID 329722 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[C:11]([C:12](O)=[O:13])[C:6]=2[O:5][CH2:4][C:3]1=[O:18].S(Cl)([Cl:21])=O>>[CH3:1][N:2]1[C:7]2[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[C:11]([C:12]([Cl:21])=[O:13])[C:6]=2[O:5][CH2:4][C:3]1=[O:18]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14771561HCID 14771561, compound

Product 1

HCID 14802114HCID 14802114, compound

Procedure

To 99 g of 3,4-dihydro-4-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid is added portionwise 285 ml of thionyl chloride at room temperature, and the system heated with reflux for about an hour. After the resultant solution is dried under reduced pressure, to the residue is distilled off under reduced pressure. To the residue is added 200 ml of benzene to make the crystals finely particulate. After collecting by filtration, the crystals are washed with benzene and dried to give 103 g of 3,4-dihydro-4-methyl-6-nitro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid chloride.

Workup

  1. temperaturethe system heated
  2. temperaturewith reflux for about an hour
  3. dry with materialAfter the resultant solution is dried under reduced pressure, to the residue
  4. distillationis distilled off under reduced pressure
  5. additionTo the residue is added 200 ml of benzene
  6. filtrationAfter collecting by filtration
  7. washthe crystals are washed with benzene
  8. customdried

Sources & evidence

ORD record
ord-43f47df6842b41808fa5e6086efe4779
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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